Chapter 2
The Dot-Com Crisis
The Stories of David Kenny, Kris Gopalakrishnan, and Raf Keustermans

Photo of David Kenny.

NEW YORK, MARCH 2000

People in the tech world were still partying like it was 1999. The Internet revolution had people from Silicon Valley to Wall Street and far beyond dreaming of a world where the new technology stood front and center, and Internet-entrepreneurs were the new billionaires. It was a self-fulfilling prophecy. In less than five years, shares in the technology stock index NASDAQ grew by more than 500 percent. On March 10, 2000, it hit an all-time high of 5,048.62 points. But that was all about to end.

For some companies, like Kris Gopalakrishnan's Infosys, the dot-com era meant a breakthrough after decades of hard work. The IT outsourcing company was founded by seven engineers in 1981, and it took them 23 years to make their first billion dollars in revenues. But it took only another two years to make the second billion, and only a year for the third billion. On the back of those successes, the company's U.S.-listed stocks exploded in value, from a little more than $1.30 in March 1999, to just under $21 in March 2000, a fifteen-fold increase.

The same was true for Digitas, an advertising company that was created in the early '80s, but that had morphed into a digital advertising agency in the mid-'90s. On March 14, 2000, it was the last company to go public in the Internet 1.0 era. The man who led the initial public offering was someone you were introduced to in Chapter 1: former Bainee David Kenny. He had left Bain after 10 years to be part of the nascent Internet boom, and had become CEO of Digitas in 1997. The IPO made him an instant multimillionaire—on paper—and valued his company at more than a billion dollars.

For other people, the Internet boom led to more pragmatic and improvised ventures. Such was the case for Raf Keustermans, a neighborhood friend of mine in Lier, Belgium. We had always played soccer together on the pitch nearby, where he had become known as “The Ginger One” because of his long, unkempt red haircut. When I was in high school, Raf was starting out as an Internet entrepreneur, setting up, among other things, an online jokes site and a chat network, after dropping out of college in his first year. He had gotten $25,000 in seed money from another neighborhood friend's uncle.

“Why don't you set up a regional news site for me,” Raf asked me one day in the summer of 2000, after listening to an online radio program a friend of mine and I were hosting called “Studio 17” (a wink to Studio 54, with 17 being the street number of my friend's house). “It's going to be the newest trend online, and we can be the first ones in the game,” he said. The summer break was just about to start, so I had no reason to say no. By the end of the summer break, we had a functioning beta site and were excited to move the project forward.

But the project didn't go forward. Instead, the Internet hype came to an abrupt end. On the stock exchange, the dot-com bubble burst, and when the tragic events of 9/11 occurred in 2001, Internet 1.0 was over for good. In Europe, Raf's Internet company dwindled. Over in New York, the shares of David Kenny's Digitas came crashing down from a share price of about $25 at its introduction, to 88 cents by October 2001—representing less than $40 million in residual valuation. In India, Kris Gopalakrishnan and his fellow co-founders saw their NASDAQ valuation go down by the billions as well, as their stock price fell from $21 in 2000, to just one-tenth of that right after 9/11. Gopalakrishnan saw his work of 20 years literally decimated, and Keustermans was left with no college degree, no money, and a company worth next to nothing. As for Kenny, he saw his virtual riches vanish in thin air and faced imminent bankruptcy, while at home he and his wife had two young girls to raise. What were these three men supposed to do next?

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In the last chapter, we saw how future leaders dealt with tough choices in uncertain times, and how they found the strength to persevere, or the courage to quit. In this chapter, we turn to other, almost inevitable types of events: What do you do when, like Raf Keustermans, what you've worked for over a number of years turns out to be worth next to nothing? What do you do when, like David Kenny, you're going through a really tough time just to keep a company afloat? Or what do you do when, like Kris Gopalakrishnan, your work of 20 years is decimated? As we'll learn from their accounts, those moments—though extremely challenging when they take place—can be the seed for success as well as modesty later on.

When I spoke to Raf, David, and Kris almost a decade and a half after the dot-com bubble burst, they could remember the episode with a smile. The NASDAQ had returned to record levels in 2015. Keustermans ended up in London, founded a social gaming company, and early in 2016, sold it to a competitor, earning his investors several million pounds. Kenny had stuck it out at Digitas and managed after a few years to sell the company to advertising giant Publicis. When we first met, he was the CEO of The Weather Company, the largest TV and Internet company for weather services globally. In 2016, he sold The Weather Company's digital arm to computer-giant IBM, and became head of its renowned “Watson” computer project. Meanwhile, Kris and his fellow co-founders all remained at Infosys, and continued to build the company despite its stock market tumble. Kris is now a billionaire and executive vice-chairman at Infosys, which is one of top IT and consulting companies headquartered in India. But the things that these three men experienced during the wondrous year 2000 and its terrible aftermath have stuck with them. So how did they get to play a part in the 2000 tech bubble? How did they overcome its adversity? And what lessons can we draw from it?

KERALA, INDIA, 1955

Senapathy “Kris” Gopalakrishnan was born in Trivandrum, the capital and largest city of Kerala, India, on April 5, 1955. Located on the southwestern coast of mainland India, and surrounded by green hills, Trivandrum was nicknamed “The Evergreen City of India” by Mahatma Gandhi. But all wasn't rosy. India had gained independence from Britain just seven years before Kris was born, and its first prime minister, Jawaharlal Nehru, struggled to find an adequate economic recipe for the nation. In Nehru's almost two decades in office, India steered a protectionist and centralist economic course, leading to what would later be known as the “Hindu rate of growth,” a per capita growth rate far below that of other Asian nations, such as South Korea and Taiwan.

It was against this backdrop of a nascent, struggling nation that Kris grew up in the 1960s. He went to a public high school in Trivandrum, the Government Model High School, and prepared to enter medical school following his parents' wishes, despite his own preference for engineering. Although he went into the entry exam confident that he would pass it, Gopalakrishnan scored just two points below the minimum to get accepted. To make matters worse, he hadn't signed up for any engineering school as a back-up plan, being so certain he would get into med school. Clueless about what to do next, the young Kris saw his self-confidence tank, Gopalakrishnan told me in 2014, as he recounted the turning points in his life. Seated in a white egg-shaped plastic chair in the Davos Congress Center, 58-year-old Gopalakrishnan, now silver-haired and wearing his signature mustache, wouldn't talk about the Internet crash of 2000–2001, when he saw billions of dollars vanish into thin air. Apparently, the med school incident had been more impactful.

“It took me three years to get my confidence back,” he said. In those three years, Gopalakrishnan studied physics at a local college in Kerala, and slowly got back on his feet. He eventually regained his self-confidence, thanks in large part to his math teacher at that time, C. C. Philip. “He saw me and believed in me when I did not,” Gopalakrishnan said. “He told me to try again, this time with his help.” It was the push the young man needed. After three years at the local college, he applied again for a more prestigious school, the Indian Institute of Technology in Madras, and passed the written engineering entrance exam. “Passing that hurdle was a turning point to rebuild confidence,” Gopalakrishnan said. “It showed me that I have what it takes to succeed. It confirmed to me that I had the ingredients for success all along.”

Surprisingly, at the end of the application process, Kris faced the same situation: although he passed the written exam, he failed the oral interview (because of his limited knowledge of the English language) and wasn't admitted to the university of his choice. But it didn't matter as much to him this time. He carved out a plan B, in the master's degree program in physics at IIT, the Indian Institute of Technology. Those studies may still not have been his preferred choice, Gopalakrishnan explained, but they did open the door to co-founding one of the biggest Indian companies of our time: Infosys.

“Looking back, chance, coincidence, and luck played an important role,” he said. “It's difficult to anticipate the future—35 years back, I could never imagine to be where I am now.” So what triggered his future?

“When I was working on my master's in physics, I took an optional course in computer programming,” Gopalakrishnan said. “I got passionate about it, and switched to computer science. It was pure chance. I did not say: this is where I need to have the big breakthrough. I just happened to be at the right place at the right time.”

He certainly was. Gopalakrishnan started studying computer science in 1977, the same year that Steve Jobs, Steve Wozniak, and Ronald Wayne founded Apple. He was working in his first job, at Patni Computer Systems, in 1980, when Bill Gates won the IBM contract that led to the development of MS-DOS, and eventually, Microsoft Windows. One year later, in 1981, Kris and six others left Patni to found an IT-company of their own: Infosys.

“When we started, many of our classmates had migrated mostly to the United States,” Gopalakrishnan explained. “But we said: ‘Hey, here are some of us that want to stay in India—let's build a business here.’”

Having no savings or family funding, the seven registered their company with only 10,000 rupees in capital, or about $250, and rented a house in Pune from which to run their company. It was all very “Apple-like,” Gopalakrishnan said. “We would share rooms, sometimes even tables. We would also get a loan and a license for our first computer, the only computer we had. We would lease it out during the daytime, and use it ourselves during the night time to save costs.”

In that first year, Infosys hired three people, mostly because of a contract it got with its first client, Data Basics Corporation in the United States. That made the company profitable from the start as well. But revenue growth was slow, and so was that of their own income.

Group photo of Infosys founders.

The founders of Infosys, with Kris Gopalakrishnan, in the early 1980s

When Gopalakrishnan's told me of the next turning point, it became clear that we had a fundamentally different perspective on the importance of time in building your career. I always assumed that time was of critical importance if I wanted to become successful; that I had no time to lose. I feared that if I “missed the boat” of a fast-track career early on, I could not become a senior executive later. Kris's story made it clear to me that this was a wrong way of thinking. He skipped almost 10 years in recounting the turning points in his career.

“The first 10 years [of Infosys] was about survival,” Gopalakrishnan said. “It was about making enough money to get around, and grow slowly. We cared more about doing things right than about doing things fast.” I couldn't imagine spending the first 10 to 15 years of my career not thinking about the next step—but he clearly did.

By 1989, he said, “we still had nothing to show. Our revenues were a million dollars, and we were with about 40 to 50 people working in the company.” (Simply put, this equates to $20,000–$25,000 in revenues per employee, or calculated in a different way, $150,000 in revenues per founder, before paying all overhead costs such as salaries.) “We talked to our former classmates, and by now, they all had a car and house. We, on the other hand, had nothing of that. We were 10 years out of university, and we lived in modest apartments.”

India as a whole, wasn't doing too great either. By 1985, India was starting to have balance of payment problems. By 1990, it was in an economic crisis. Around that time, the Infosys co-founders got an offer to be bought out. It caused some serious doubts. “Many said: ‘Maybe we should sell and go,’” Gopalakrishnan recalled. “But our chairman, Narayan Murthy, told us he'd buy us out and continue on his own if he had to.” That was the turning point. “Once he had said that, we decided to stay together and continue. We told ourselves to aim for an IPO in three years, and scale up the business significantly from there. And that's how it all worked out.”

Considering the macroeconomic environment of India at the time, it's easier to understand why Gopalakrishnan is such a believer in “being at the right place at the right time.” In 1991, 45 years after India regained its independence, and after the same number of years of “Hindu years of growth,” the country's leaders finally decided the time had come to open up to the world. In a series of liberalizations, India moved toward more of a market economy, away from the centralization initiated by Nehru in the 1950s, and opened up its capital markets for foreign investors. It paved the way for Infosys as well. In February 1993, effectively four years after its founders had decided to resist a private buyout, the company went public and sold its shares at 95 rupees a piece, which was 75 rupees higher than the book value.

The IPO made all of the founders millionaires, and gave them redemption for the more than 10 years in which they had had nothing to show. But the IPO was just the beginning. The founders took all the money from the IPO and invested it back into the business instead of cashing it in. That, together with the dot-com boom, which by the mid-1990s started to really gain steam, led to a period of exponential growth. “The Internet bubble created a huge demand for software services,” Gopalakrishnan recalled. “We grew by 100 percent or more every year.” It wasn't just their revenues, which doubled every year—their stock value followed suit. By 1994, the stock price had surged to 450 rupees. By March 1999, when the company started trading on the Indian stock exchange as well as on NASDAQ, the stock traded at more than 3,000 rupees in India, and opened at around $1.46 in New York. A year later, as the NASDAQ reached its zenith, the U.S.-listed stocks exploded to almost $21, whereas on the Indian exchange, the share had peaked earlier that year at 16,855 rupees per share—more than the entire starting capital of the company in 1981. Infosys was one of the 20 largest companies listed on the NASDAQ, and Gopalakrishnan was a billionaire.

BOSTON, 1997

At the same time that Infosys was going through its astronomical growth phase, direct marketing firm Digitas was reinventing itself online to capture its own share of the dot-com boom. To guide the company through that bold strategic shift, it counted on a man you were introduced to previously: David Kenny. Could the General Motors manager turned management consultant morph into an Internet CEO next?

“What happened? Internet happened!” Kenny replied when I asked him what triggered his switch to Digitas in 1997. “AOL started, Yahoo, Minitel in France… And I thought: if this takes off, this will be huge.”

More specifically, in 1995, Kenny met Jerry Yang, who was CEO of Yahoo at that time. Yahoo had only about a hundred employees then, but it was already a fast-growing company. “I made the decision to switch to the Internet industry a year later,” Kenny said. “I had an idea in my head that the Internet would really help say for each person what was interesting for them. Now, we know this as retargeting.”

While Yang and others were already starting to discover the Internet, most marketing firms were still focused on the real world. That was the case for Michael Bronner, the founder of Digitas. Kenny, who knew Bronner from a previous consulting assignment, saw an opportunity. One night, Bronner and Kenny had dinner in Boston, and talked about how the Internet could change everything, which might require some fresh impetus in the company. It turned out to be a turning point. The next day, Kenny recounted, “Bronner called me and said I was right about the need to delegate, and about embracing the Internet more. ‘You need to come in and run the company,’ he said, and literally for months, I told him I wasn't sure. But he was determined I run the company, and in the end, we struck a deal.”

Having been a Bain partner for 10 years, this was a lot for Kenny to give up, especially after all he had been through with the company. “People had called me before for other jobs,” Kenny said, but those jobs hadn't been interesting. Now however, he was ready for it: “My risk profile was right.”

In order to understand where Kenny was at this point in his life, let's take a pause to explore what exactly a risk profile is and how it can be “right” for different job changes throughout your career. When we start our careers, switching from one job to another doesn't carry a lot of risk. After all, when you're young, and you have neither a work history nor a family, there's nothing much to lose. Such was the case for Kenny when he switched from GM to Bain: It was a great opportunity—period.

After about five to seven years, things start to change for many people. By the time you're in your late twenties or early thirties, chances are you're getting married and starting a family, which might not seem like a great moment to make big career changes. It's often after you're settled in your family life and you have solid finances that career changes surface again.

In a way, David Kenny was no exception. Having married right after business school, their first daughter was born in 1993, and their second one in 1996. “Right when we got children, I couldn't just go and be an entrepreneur,” Kenny said. “You sense a different level of responsibility.” But by 1997, having been a partner at Bain for several years, and with his wife having worked in venture capital, the financial outlook for Kenny and his family was positive, and their personal life was in balance. They had paid off their mortgage and had saved money for the children to go to college. Kenny and his wife deemed the time right to make a career move. “I didn't feel it was irresponsible, because we didn't have a mortgage and saved money. We lived rather conservatively. That was crucial: I never had to make a decision based on the financial aspect of it. I could make it based on what I love.”

Moving out of consulting would also allow Kenny to feed his intellectual curiosity. Despite the hands-on approach of Bain, sitting in the driver's seat as CEO would still be a different experience. “I figured that after having done Bain for 10 years, I won't learn as much in the future as I did in the last 10 years.” Kenny also believed that he would be home more often than when he was a consultant, which had involved a lot of travel (although that prediction didn't actually materialize). Kenny negotiated a deal with Bronner about his salary and stock, and he and his wife decided that he would take the CEO job while his wife would stop working and take charge of their family life. “It only worked because it was a team decision,” Kenny said. “It certainly helped to have a stable family, and my wife is a large factor in my success. She ran the finances, she ran our investments, and she ran the household. That made life manageable. It was a real division of labor, and it worked, because we both loved it.”

In the following years, Kenny had a “great” time, because “we really did figure out retargeting with Digitas.” The pinnacle came on March 14, 2000, when Digitas went to the stock exchange. “The NASDAQ was at 5012, I'll never forget it,” said Kenny. “The company was valued at $2.8 billion. That's the richest I've ever been.”

LIER, BELGIUM, 2000

As Gopalakrishnan and Kenny were counting their riches, Raf Keustermans was among those attracted by the success stories and wanting a piece of it. Four years earlier, at age 16, he had made his first entrepreneurial steps by organizing parties at the local church's events hall with two other neighborhood friends, earning about $500 per party. In the years that followed, he and his pals went on to organize ever larger parties for up to 1,500 people at the largest event hall in Lier, the Belgian town about 35 miles from Brussels that we both lived in, which had a population of about 30,000 at the time. It was exciting and new for Keustermans, who didn't come from a family of entrepreneurs, but unnerving for his parents, who would have preferred it if their son took a safe summer job at a local hamburger restaurant.

For Keustermans, it was only the beginning. “We felt on top of the world,” he said. “Organizing that first party was about making money and having people look up to us.” By the time he graduated from high school, Keustermans had more than half a dozen parties under his belt, some of which had been successes, others of which had been failures, but all of which had him longing for more. “Those first successes, those people who look at you as the man in charge, the reputation you get and the ego boost that stems from it…it's all very appealing, and makes you want to experience more of the same,” Keustermans said.

Once he was in college, studying political science and mass communications, Keustermans couldn't be bothered by the academic approach of his professors, and the many hours spent in classrooms and study rooms, without getting a taste of what the classes would mean in real life. He passed only about half of his exams, deferring the others to the summer, and then failed half of those as well. “It wasn't ideal,” Keustermans told me when we caught up over the phone 15 years later. “I was quickly distracted, wasn't very feeling 100 percent at my place, and didn't think much of most of my classmates either.”

After a year, Keustermans decided to give “real life” a chance—and went looking for a job. The mother of a mutual friend of ours arranged for an unpaid internship for him in the media world, and then Keustermans quit college and joined an Antwerp-based advertising agency full-time. Being by far the youngest person at the agency, Keustermans got assigned to the online campaigns. “Online” was still a very small business in Europe, but as we saw with Kenny, it was a very promising business elsewhere. “Obviously, I wasn't going to be an account director anytime soon,” he said, “but because I was the youngest of the team, it seemed to make natural sense to put me on the Internet campaigns.”

It was the time, he recalled, in which stories from across the ocean such as the Digitas IPO made him dream about what could be. “You heard the stories of students selling their websites for millions, and obviously, I followed those stories,” he said. Dreaming of similar riches, Keustermans started a website for telling jokes, and when that wasn't an immediate success (not everyone can be “Funny or Die”), an IRC chat portal called Cyganet. The uncle of another mutual friend of ours, who was equally attracted by the success stories from the dot-com boom, decided to invest 25,000 euro in the company. Soon Cyganet was expanding rapidly, even though it had only two employees: Keustermans as the commercial brain, and his Ghent-based partner as the technical wizard.

It was around that time that Keustermans asked me to make a regional news website for him.

THE UNRAVELING

The three protagonists of this chapter didn't have a lot of time to enjoy their riches in 2000.

David Kenny, most notably, was a multimillionaire for only 10 days. In the month following Digitas's IPO, the NASDAQ lost a third of its value, and so did the valuation of its companies, including Digitas and Infosys. But the worst was yet to come. In 2001, the year of the devastating attacks on the World Trade Center Twin Towers in New York, the NASDAQ index again lost more than half of its value. By October 9, 2002, almost exactly one-and-a-half years after it had reached its all-time peak, the NASDAQ closed at its lowest level ever: 1,114 points. As a whole, the stock index had lost a massive 80 percent of its value, and hundreds of billions of dollars had vanished into thin air. Many companies went bankrupt, got sold for a fraction of their peak value, or simply ceased operations. The consequences for Kris Gopalakrishnan, David Kenny, and Raf Keustermans were dire, but because of the different stages that their companies and they themselves were in in their lives, they all experienced the bursting of the bubble differently, reacted differently, and learned different things from these circumstances.

The Lessons Learned from Senapathy “Kris” Gopalakrishnan

Gopalakrishnan had known no riches for most of his life, and had to work for nearly a decade to achieve even minor success with his Infosys. It was only after those initial years of struggling that his company went through a decade-long exponential growth phase. Even with his Infosys shares losing more than 90 percent of their value since their peak moment on NASDAQ, they had still grown in value since their introduction on the U.S. market in early 1999, and were still worth more than 100 times their initial book value in 1993. Although Gopalakrishnan was not a billionaire anymore, he was still a millionaire, and his company was still in decent shape compared to many of the true dot-com bubble companies.

It was probably for this reason that Gopalakrishnan didn't mention the dot-com crash as being an important turning point when we talked. He merely mentioned it indirectly, saying that “the Internet bubble created huge demand for software services [such as our own],” and that “we took advantage of that and grew very fast.” What he did say, and even stressed, was that in the many early years of Infosys, as the founders went through tough times, they were able to “ready the company for high growth later on.” He said that during the company's first years “it was not yet about size; it was about the work we did. And that was an important decision, because it forced us to do the things right, and to do the right things. During that time, we invested heavily in education, training, and quality systems.”

That focus on “doing things right” is what later enabled Kris and his fellow founders to grow the company to global dimensions, and to weather the storm when it occurred. Looking back, Kris said: “In the beginning, we were not in it for the money. We wanted to build something to be proud of. We were willing to wait a little bit. If you want to build an institution, it takes time. If you want to get instant gratification or money, on the other hand, it will be very rare to build a successful business.”

In the end, Gopalakrishnan and his peers built Infosys into a global IT powerhouse. Infosys survived and thrived, and so did Gopalakrishnan. In 2007, he took the helm as CEO at Infosys, a position he kept for four years, and managed to double the company revenues from about $3 billion to $6 billion. He did so as the next crisis, the Great Recession of 2007–2008, was unfolding. Nowadays, Kris is executive vice-chairman. At the time of this writing, Infosys had doubled its revenues to over $8 billion, and its shares were trading at around $17, just 20 percent shy of their all-time peak in 2000. Gopalakrishnan is once again a billionaire. Infosys has gone from seven founding employees in 1981, to more than 179,000 today. In the United States, it is one of the top five companies issuing visas.

Kris remained calm when I asked him about the secrets to his success. Having seen the tide turn so many times over the course of his career, he pointed to “luck,” as one of the clues to his success. Rather than talk about material success or titles, Gopalakrishnan talked about success as something much more intangible. “People say: ‘Success is if you can marry your passion with your job,’” he told me. “And when I look back, that is what has happened. I was fortunate enough to be part of something that is transforming society. Infosys is part of a technological transformation, and it is part of the change in India, which is going from a third-world country to one of the fastest-growing economies in the world. Today, India is known for its software, for its professional skills, and things like that. It's very satisfying to be part of all [this], and to be able to step back and say, ‘This is how we are transforming lives, businesses, countries, and how we have helped to look at everything that we do in a different way.’” Kris's lessons, as I see it, are that before all else, you must believe in yourself; that you have to look for satisfaction in the present and your current activities; and that you should recognize the role of circumstances and of other people when you eventually do find success.

The Lessons Learned from Raf Keustermans

Keustermans wholeheartedly agrees with Gopalakrishnan that it takes time to build an institution. “You need to know whether ‘you want to king or you want to be rich,’” Keustermans said as he looked back at his career. As he is once again building an Internet company, Keustermans now aims to be “king,” meaning he prefers to build a relevant and impactful company, before aiming to get rich. But back in the early 2000s, he was the embodiment of the money-driven young gun. It is probably why his experience and learnings from the dot-com era are so different than those of Gopalakrishnan.

After working on his CygaNet company for another year without much success, Keustermans and his business partner decided to call it a day in 2003. Many of his clients had closed their doors in the direct aftermath of the crash, and the pool of profitable clients became smaller as time went by. “At the end, our operations had become such a mess that we were happy it was over,” Keustermans told me without much regret. He sold the company to a competitor and recovered about half of his investors' money. He once again had to start over, with no successes and no college degree to back him up. “I had to take a step back,” Keustermans said. “We had learned a lot with Cyganet, but at the end of the day, you have to put bread on the table, and we hadn't.” There was no doubt what the whole dot-com bubble had meant for him: a failure and a setback. (As for the regional news website that he and I were planning, it never materialized, and we ultimately shelved the project.)

After that, Keustermans continued to work as an independent contractor for ad agencies, “doing a temporary contract here, a maternal leave replacement there,” he said. In those years, he learned to sell himself and to persevere. “I had to take one step backwards in order to take two steps forward,” he said. “You need to go through adversity, to hit a wall and get back up again. You have to understand that not everything will work and that everything can't be fun.”

Then, after a few years, Keustermans was ready to take his two steps forward. He started working with Mr. Bookmaker, an online sports betting site, and stayed with the company when it was bought a year later by Unibet, a much larger competitor. This time, Keustermans had joined a company for which the Internet wouldn't turn out to be a bubble. Unibet and competitors like bwin would gain notoriety in Europe, partly because of their unclear legal status in many European countries, and partially because they started shirt-sponsoring some of the biggest sports teams on the continent. Bwin became the main sponsor of European soccer giants like Real Madrid of Spain and A.C. Milan of Italy. Unibet, among other ventures, set up an elite professional cycling team. Keustermans grew quickly within the ranks of the fast-growing company, just as many others did, following the logic of a rising tide that lifts up all boats. Within a year, he was transferred to the London offices of the firm, and received another five or six promotions in three years. “In that time, I saw how a company can outright explode,” Keustermans told me. “We grew by double digits every month and doubled our revenues every six months. There were constantly new people around us, and everything we did turned into gold.” On top of that, switching from the parochial Flemish countryside to the cosmopolitan London urban area made a big impact as well. “Young people from all over Europe moved to Wimbledon to work for Unibet. It created a very special atmosphere, as both the company and all of us working for it were new kids on the block.” With the Unibet experience under his belt, Keustermans consequently spent a year and a half doing the marketing for Playfish, an Internet game developer. Electronic Arts, known for Madden NFL and the FIFA series, had just acquired the company and wanted to develop it. It taught Keustermans about mobile gaming, virtual currencies, and social media like Facebook.

Looking back, those consecutive assignments completed his skill set and network. After a year and a half at Playfish, Keustermans in 2011 was ready to give startup life another go. Alongside two colleagues from Playfish, Gerald Tan and Jodi Moran, he set up Plumbee, a social casino company that specialized in slots games on Facebook. Gerald and Jodi brought in financial and technological know-how, and Raf supplied the marketing knowledge. This time, it became almost an overnight success.

In terms of technology, it was a culmination of a decade working at Cyganet (startup), Unibet (casino), and Electronic Arts (social gaming). In terms of building a team, it was in a way an encore to the Unibet startup culture, bringing together dozens of people from all over Europe to reside and work in London, living the “work hard, play hard” mantra. And in terms of money, it was a venture-capital story from the book: Keustermans and his team collected $1.4 million in the seed round, amassed another $15 million in the second round, and continued to invest profits in the company afterwards, so as to keep building scale. As of the time of this writing, Keustermans said the company was profitable, its signature Facebook app “Mirrorball Slots” had 1.2 million likes (half a million more than my employer, the World Economic Forum), and its Slots game had brought in more than $50 million over the course of its lifetime.

What were the lessons that Keustermans learned from the dot-com crash, and his subsequent long way to making it to the top? “Success is a combination of luck, finding the right environment to grow in, and perseverance,” he said. Regarding luck, he said that “of course, working hard is an important factor, but if you look back on my course, and the road that brought me to Unibet, EA, and then Plumbee, you have to admit that a part of it is also plain luck. No more and no less. The luck I had was that I found this job at Mr. Bookmaker, and got moved to London when it was bought by Unibet. In another life, I might have still been selling ads in Belgium, and have worked just as hard.”

On the right environment, he referred to his time at Unibet and EA in London, and how he met, among others, his Plumbee co-founders. “First, you want to work in an environment where you're inspired,” which could be anywhere and in any sector, as long as there are the right people. But second, “You shouldn't underestimate the geographical factor,” he said. “You'll be more likely to meet the right people in New York, San Francisco, Berlin, or London than in a village in the province. So if you're not born there, like me, you should move there.”

And on the perseverance and hard work, he said, “I know very few successful people who don't work hard and persevere.” In part, he said, it may also have to do with making sacrifices. “I don't have a family and children, so I have a different life than most. I don't have regrets, but I do hear others CEOs saying often how they wish they had spent more time with their kids. But in the middle of the action, you don't think about that. Today I got up at 5 a.m. for a meeting in Guernsey, then had a flight back, had many e-mails to answer, phone calls to make, and a board meeting to prepare. Maybe in five years, I'll say to myself that I should have taken it easier, but for now, I don't have regrets.”

The final reward came in February 2016: Keustermans sold his company to a competitor, allowing him to cash in several million dollars for his investors—and a nice (but undisclosed) sum for himself, too, next to securing employment for his employees. As I was preparing to meet him in London before submitting this chapter, I saw on Facebook that he had booked a “long overdue holiday” to New Zealand. After all the work, there was time for relaxation at last.

The Lessons Learned from David Kenny

If Gopalakrishnan was able to remain Zen during the dot-com crash because of his decades of patiently building a company, and Keustermans was able to move on quickly because he was just coming around the corner, David Kenny was stuck in the middle. He had amassed 20 years of professional experience and had plenty to show for himself, but all that was worth nothing when in the months following the IPO of Digitas, the stock price came crashing down from $24 at introduction to $.88 during the days following September 11, 2001. During that time, the very existence of Kenny's company came into play, and with that, his reputation as CEO and his net worth as an investor (he owned 12 percent of the stock).

As it was for so many people, 9/11 was a very unsettling experience for Kenny. Digitas clients such as American Express were among the companies leasing office space in the Twin Towers, and Kenny knew people who lost friends and colleagues in the attack (though no one Kenny knew personally was killed). Kenny himself was in San Francisco when the tragic events of 9/11 happened, and he couldn't get home for a number of days due to the closing of the air space.

“I was scared, my family was scared, the people in the company were scared, and I had to stay [in San Francisco] and take one step in front of the other.” The reason, of course was the financial fall-out from 9/11. “Almost immediately, I went to look for cash,” Kenny said. “I needed to make sure we had enough cash to pay for the payroll. The stock price didn't matter—all that mattered was cash.”

But of course, the stock price did matter, and so did the underlying financial numbers of Digitas. And those were dire. “When the markets reopened on September 12,” Kenny said, “everyone thought Digitas was finished, and the institutional investors, including Fidelity and Vanguard, sold off all or most of their stock.” For the company, the phase of survival had started. The hardest moment came a month later, on October 11, 2001. On that day, which was supposed to be a celebratory one, given that it was his 40th birthday, Kenny had to fire a third of his personnel and talk to the shareholders about the (presumably really poor) quarterly results.

To get through that period mentally, Kenny said, he was happy he could go back home to spend time with his family. “It was important for me to go with the kids,” he said. “They were so young, and didn't have a clue what was going on. That helped, because it gave me a different perspective.” Physically, Kenny persevered because of his health and fitness regime. “I [went] to the gym every day, and I watched what I [ate] and [drank],” he said.

Kenny also had already experienced the near-demise of Bain, and had learned from Orit Gadiesh and Mitt Romney that it was important to keep in mind what the “true north” of his company was. “I was completely composed when the crash happened,” he said. “Sure I was disappointed, but you have to be very careful to not let the stock market decide your own idea of value.” So he held on to what he had installed as the core principles of the company (“One with the Client,” “Experts Inspiring Experts,” and “Best Getting Better”) and felt he had energy for everyone at the company: “I had to be tough,” he said, “because others were breaking down. I was focused on what was needed to be done to get us in the right place, and I couldn't blink.”

Gradually, the company got back on its feet, as did the U.S. economy as a whole and the tech sector in particular. Kenny stayed on to lead the company for another five years after that, and in 2006, he sold Digitas, along with his shares in the company, to French advertising giant Publicis. By then, the company's valuation was back at $1.2 billion, almost half its peak at introduction, but more than 10 times what it had been worth right after 9/11.

As we talked about the lessons he has learned thus far during his career, particularly the dot-com era, Kenny told me his most important learning was how to deal with failure. “Even when you fail, the sun comes back up the next day,” he said. “I learned that lesson at GM, where major restructurings happened while I was there, and I saw it again at Bain.” And at Digitas, he could apply those lessons from failure himself. Those experiences strengthened him in the conviction that “how you handle setback is more important than anything.” For that reason, he said, “I just don't think you should be afraid of failure. You should be afraid of not learning. That's important.”

So how does his story continue? After the dot-com era, Kenny stayed on for a while at Publicis, but then realized how being a non-French executive in a French company would obstruct him from ever becoming CEO, and he left. He accepted an offer to become President of Akami, an IT company making the “pipes and plumbing” of the Internet. Soon though, he realized it was not the exciting job he had hoped for. And so, in 2010, after a career of 30 years, and with never having made a CV, Kenny found himself without a job for the first time in his life. Having by now a net worth of well over $100 million, and having proven himself as CEO in the harshest of circumstances, Kenny could afford to be transparent about his unemployment. He played open cards on LinkedIn and called the interim period he was in his time as “President of Deciding What's Next.” And what came next for Kenny was heading The Weather Company.

Having seen that curious title on his CV, I also asked Kenny about what he looked for in a CV when hiring a person. He told me he focused on three things:

  • Are you a good person? Are you honest, curious, and fun to hang out with?
  • Are you passionate? Do you believe in what you're doing?
  • Have you had a setback? Did you get stronger as a result?

“I'm very wary of people that had a charmed privileged life,” Kenny said “People that went to the right schools, only had successes, or only talk about successes: what that tells me is that they haven't taken enough risks. I would say most of the CEOs I know have strong convictions, and most of them have made mistakes. Until you've done that, you can't lead an organization.”

Kenny, on the other hand, can. In January 2016, after some four years as CEO, Kenny completed the sale of The Weather Company to IBM. With a price tag of around $2 billion, it was the second time in his career that Kenny managed to sell a “unicorn”: a tech company worth more than a billion dollars. IBM was mostly interesting in buying The Weather Company for its rich collection of weather data. For Kenny, the sale meant another leap in his career: He became head of IBM's Watson platform business.

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